Refractive Index Changes of Amorphous Diarylethenes Containing 2,4-Diphenylphenyl Substituents

Kim, Myeong-Suk; Maruyama, Hideki; Kawai, Tsuyoshi; Irie, Masahiro

doi:10.1021/cm030304v

Cited by 93 publications

(48 citation statements)

References 34 publications

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“…Photochromismisalight-initiated, nondestructive process resulting in reversible transformation between two isomeric forms that have remarkable differences not only in their absorption spectra, but also in various physical and chemical properties, such as fluorescence [1,2], refractive index [3,4], chiral [5], magnetic [6], oxidation-reduction potential [7][8][9], and geometric structure [10]. Among the photochromic compounds, diarylethene derivatives are the most promising candidates for potential application to opticalmemorymedia and optical switches because of their thermal stability and fatigue resistance.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of [1-(2,5-dimethyl-3-thienyl)-2-(2-ethyl-5-formyl-3- thienyl)]- 3,3,4,4,5,5-hexafluorocyclopentene, C18H14F6OS2

Fan¹

2012

Zeitschrift für Kristallographie - New Crystal Structures

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C 18 H 14 F 6 OS 2 ,monoclinic, P2 1 /c (no.14), a =12.720(2) Å, b =9.029(2) Å, c =16.794(3) Å, b =99.914(2)°, V =1900.1 Å 3 , Z =4,R gt (F) =0.0478, wR ref (F 2 ) =0.1418, T =291 K. Experimental detailsAllHatoms attached to Cwerefixed geometrically and treated by aridingmodel with C-H=0.96Å(methyl)or0.93 Å(aromatic) with U iso (H) =1 .2 U eq (aromatic)o rU iso (H) =1 .5 U eq (methyl). The Fa toms attached to the Ca tomsi nc yclopentene ring are disordered over two crystallographic sites. The occupancy factors of the two positions were refined using an overall isotropic thermal parameter and by restraining the sum of the occupancy to remain equalt o1 .0. The ratio between the two occupancies was found to be 0.89/0.11. The C-F distances were restrained using SADI (SHELXL-97) instructions and similar U ij restraints as well as rigid bond restraints were usedi nt he final refinement cycles. Source of materialThe(2,5-dimethyl-3-thienyl)perfluorocyclopentene (1.52g,5.0 mmol) was reacted with 4-bromo-5-ethyl-2-(1,3-dioxolane) -thiophene (1.32 g, 5.0 mmol) in the presence of n-butyllithium (2.5 Minhexane, 2.0 ml, 5.0 mmol) at 195 Kunder anitrogen atmosphere. After an hour, the reaction was quenched by the addition of water. The solid product was purified by column chromatography on silica using petroleum ether as the eluant to give the compound {1-,4,4,5,5-hexafluorocyclopentene (1.17 g, 2.50 mmol, yield 50%). This compound (1.17 g, 2.50 mmol) and p-toluenesulfonic acid (0.4 g) were dissolved in mixture of water (30 mL) and acetone (90 mL); 2mLpyridine was added into the mixture and reaction mixture was refluxed for 24 h. After stopping the reaction, the mixture was washed sequentially by aqueous NaHCO 3 andwater. Theorganic layer was dried over anhydrousNa 2 SO 4 ,filtrated,and evaporated. Thecrude product waspurifiedbycolumnchromatography on SiO 2 using ethyl acetate and petroleum ether mixture (v/v=1/6) as the eluent to give 0.90 gofthe title compound ( figure, top) [7][8][9], and geometric structure [10]. Among the photochromic compounds, diarylethene derivatives are the most promising candidates for potential application to opticalmemorymedia and optical switches because of their thermal stability and fatigue resistance. Hence, the synthesis of diarylethene derivatives and investigation of their structural featuresare of both scientific andpracticalinterest. Themolecular structure (1o) is shown. In the cyclopentene ring, it is clear that the C8-C12 bond is adouble bond, while the others in the ring are single bonds. The two thiophene rings are linked by the C8=C12 bond. The methyl and ethyl rings are located on opposite sides of the double bond and are directed trans relative to the thiophene planes, as reflected in the torsion angles 127.69°for C11-C12-C13-C14 and135.23°for C4-C3-C8-C7. The dihedralangle betweenthe main centralcyclopenteneringand adjacent thiophene ring are 54.0°for S1/C1-C4 and 53.5°for S2/C13-16. The conformation leads to aC4-C14 separation of 3.664 Å. This distance is short enough, the...

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Section: Discussionmentioning

confidence: 99%

Crystal structure of [1-(2,5-dimethyl-3-thienyl)-2-(2-ethyl-5-formyl-3- thienyl)]- 3,3,4,4,5,5-hexafluorocyclopentene, C18H14F6OS2

Fan¹

2012

Zeitschrift für Kristallographie - New Crystal Structures

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“…In this system, the changes in the electronic patterns responsible for the changes in color also result in variations in other practical physical properties such as luminescence, [1][2][3][4][5][6][7][8] electronic conductance, [9][10][11] refractive index, [12,13] optical rotation, [14,15] and viscosity. [16,17] The photomodulation of these properties has the potential to advance optoelectronic technologies such as information storage system and actuators.…”

Section: Introductionmentioning

confidence: 99%

High‐Content Pendant Photochromic Copolymer with Dithienylethene/Fluorene 2:1 Mole Ratio

Tian

2005

Macro Chemistry & Physics

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Summary: Two photochromic dithienylethene units were incorporated into one fluorene unit as a monomer and the mole ratio of photochromic unit/repeat unit reached to 2:1 using this monomer. The content of dithienylethene component in the polymer could be improved effectively by polymerization of this monomer, which contains more than one dithienylethene units. All the starting materials concerned in the synthesis are commercially available and so the synthesis could be performed on a large scale. The polymer obtained by typical palladium‐catalyzed Suzuki coupling reaction is photochromic both in solution and in solid state and possesses good solubility. The photochromic and photomodulation luminescence properties of the polymer are also presented.

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“…Suitable processing methods have to be applied to guarantee good optical properties in thick filters. The second approach consists in the synthesis of photochromic materials that afford amorphous films, i. e. photochromic polymers both sidechain [21][22][23][24][25][26][27][28][29] or main-chain [30][31][32][33][34][35][36], small molecules with bulky groups that prevent crystallization [37][38][39][40], sol-gel matrices [41]. In these cases the concentration of the active moiety can be markedly increased and high contrast can be obtained in relatively thin films.…”

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confidence: 99%

Control of optical properties through photochromism: a promising approach to photonics

Bianco

Perissinotto

Garbugli

et al. 2011

Laser & Photonics Reviews

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In this work studies on photochromism for optics and photonics are reviewed. The versatility of organic chemistry gives photochromic materials wide opportunities for several applications that range from tunable filters and gratings, to refractive-index modulators for optical fibers and communications, to optical memories and sensors. Moreover, novel results on efficient modulation of amplified emission in a conjugated polymer/photochromic system are presented. Credit for the background image (WR 25 and Tr16-244, open cluster Trumpler 16): NASA, ESA and Jesús Maíz Apellániz

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Refractive Index Changes of Amorphous Diarylethenes Containing 2,4-Diphenylphenyl Substituents

Cited by 93 publications

References 34 publications

Crystal structure of [1-(2,5-dimethyl-3-thienyl)-2-(2-ethyl-5-formyl-3- thienyl)]- 3,3,4,4,5,5-hexafluorocyclopentene, C18H14F6OS2

Crystal structure of [1-(2,5-dimethyl-3-thienyl)-2-(2-ethyl-5-formyl-3- thienyl)]- 3,3,4,4,5,5-hexafluorocyclopentene, C18H14F6OS2

High‐Content Pendant Photochromic Copolymer with Dithienylethene/Fluorene 2:1 Mole Ratio

Control of optical properties through photochromism: a promising approach to photonics

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